Guvacine (BioDeep_00000000885)

   

Chemicals and Drugs natural product


代谢物信息卡片


3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-

化学式: C6H9NO2 (127.0633)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(not specific) 50%

分子结构信息

SMILES: C1CNCC(=C1)C(=O)O
InChI: InChI=1S/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9)

描述信息

Guvacine is a alpha,beta-unsaturated monocarboxylic acid that is nicotinic acid which has been hydrogenated at the 1-2 and 5-6 positions of the pyridine ring. It has a role as a plant metabolite and a GABA reuptake inhibitor. It is a beta-amino acid, a tetrahydropyridine, an alpha,beta-unsaturated monocarboxylic acid, a pyridine alkaloid and a secondary amino compound.
Guvacine is a pyridine alkaloid found in the Areca nut (also known as the Betel nut). It is an experimental drug with no approved indication. Experimental studies are still being investigated to determine all of the physiological effects and mechanisms of action of guvacine. Currently it has been determined that guvacine is a specific GABA reuptake inhibitor with no significant affinity at GABA receptors.
A alpha,beta-unsaturated monocarboxylic acid that is nicotinic acid which has been hydrogenated at the 1-2 and 5-6 positions of the pyridine ring.

同义名列表

24 个代谢物同义名

3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-; 1,2,5,6-Tetrahydro-pyridine-3-carboxylic acid; 1,2,5,6-Tetrahydro-3-pyridinecarboxylic acid; 1,2,5,6-tetrahydropyridine-3-carboxylic acid; 1,2,3,6-tetrahydropyridine-5-carboxylic acid; 1,2,5,6-Tetrahydronicotinic acid; QTDZOWFRBNTPQR-UHFFFAOYSA-N; Guvacine hydrochloride; guvacine hydrobromide; Spectrum2_001474; Spectrum3_001511; Spectrum5_000606; Spectrum4_001753; Lopac0_000571; GUVACINE [MI]; BPBio1_000838; DivK1c_006904; KBio1_001848; KBio3_002681; KBio2_001906; KBio2_004474; KBio2_007042; guvacine; Guvacine



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

12 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 7 CA1, CA3, CCNB1, CDK1, CDK2, GAD1, SMAD2
Endoplasmic reticulum membrane 1 CDK1
Nucleus 5 CCNB1, CDK1, CDK2, SMAD2, TGFBR1
cytosol 6 CA1, CA3, CCNB1, CDK1, CDK2, SMAD2
dendrite 1 SLC6A6
centrosome 3 CCNB1, CDK1, CDK2
nucleoplasm 4 CCNB1, CDK1, CDK2, SMAD2
Cell membrane 7 SLC36A1, SLC3A1, SLC6A1, SLC6A12, SLC6A6, SLC6A8, TGFBR1
Multi-pass membrane protein 5 SLC36A1, SLC6A1, SLC6A12, SLC6A6, SLC6A8
Golgi apparatus membrane 1 MGAT1
cell cortex 1 GAD1
cell surface 3 SLC6A1, TGFBR1, THBS1
Golgi apparatus 1 MGAT1
Golgi membrane 1 MGAT1
lysosomal membrane 1 SLC36A1
neuronal cell body 2 SLC6A1, SLC6A6
presynaptic membrane 1 SLC6A1
Presynapse 2 SLC6A1, SLC6A12
endosome 2 CDK2, TGFBR1
plasma membrane 8 GAD1, SLC36A1, SLC3A1, SLC6A1, SLC6A12, SLC6A6, SLC6A8, TGFBR1
presynaptic active zone 1 GAD1
Membrane 11 CCNB1, CDK1, MGAT1, SLC36A1, SLC3A1, SLC6A1, SLC6A12, SLC6A6, SLC6A8, SMAD2, TGFBR1
apical plasma membrane 4 SLC36A1, SLC3A1, SLC6A6, SLC6A8
axon 1 SLC6A1
basolateral plasma membrane 2 SLC6A12, SLC6A6
extracellular exosome 5 CA1, CDK1, MGAT1, SLC3A1, THBS1
Lysosome membrane 1 SLC36A1
endoplasmic reticulum 2 SLC36A1, THBS1
extracellular space 2 THBS1, THPO
perinuclear region of cytoplasm 2 GAD1, MGAT1
Cell junction, tight junction 1 TGFBR1
bicellular tight junction 1 TGFBR1
mitochondrion 2 ABAT, CDK1
protein-containing complex 1 SMAD2
Single-pass type I membrane protein 1 TGFBR1
Secreted 2 THBS1, THPO
extracellular region 2 THBS1, THPO
mitochondrial matrix 3 ABAT, CCNB1, CDK1
transcription regulator complex 2 CDK2, SMAD2
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 2 CDK1, CDK2
external side of plasma membrane 1 THBS1
Extracellular vesicle 1 MGAT1
Secreted, extracellular space, extracellular matrix 1 THBS1
midbody 1 CDK1
Single-pass type II membrane protein 2 MGAT1, SLC3A1
postsynaptic membrane 2 SLC6A1, SLC6A6
Apical cell membrane 3 SLC36A1, SLC3A1, SLC6A8
Cytoplasm, perinuclear region 1 MGAT1
Membrane raft 1 TGFBR1
GABA-ergic synapse 3 GAD1, SLC6A1, SLC6A6
extracellular matrix 1 THBS1
sarcoplasmic reticulum 1 THBS1
collagen-containing extracellular matrix 1 THBS1
secretory granule 1 THBS1
receptor complex 1 TGFBR1
chromatin 1 SMAD2
cell projection 2 SLC6A12, SLC6A6
mitotic spindle 1 CDK1
plasma membrane protein complex 1 SLC6A6
brush border membrane 1 SLC3A1
spindle pole 1 CCNB1
chromosome, telomeric region 2 CDK1, CDK2
Basolateral cell membrane 1 SLC6A12
microvillus membrane 1 SLC6A6
nuclear envelope 1 CDK2
platelet alpha granule 1 THBS1
endoplasmic reticulum lumen 1 THBS1
male germ cell nucleus 1 CDK2
platelet alpha granule lumen 1 THBS1
axon terminus 1 GAD1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 MGAT1
outer kinetochore 1 CCNB1
vesicle membrane 1 GAD1
Cajal body 1 CDK2
heteromeric SMAD protein complex 1 SMAD2
SMAD protein complex 1 SMAD2
spindle microtubule 1 CDK1
condensed chromosome 1 CDK2
Nucleus, Cajal body 1 CDK2
inhibitory synapse 1 GAD1
X chromosome 1 CDK2
Y chromosome 1 CDK2
activin responsive factor complex 1 SMAD2
cyclin-dependent protein kinase holoenzyme complex 2 CDK1, CDK2
cyclin E1-CDK2 complex 1 CDK2
cyclin E2-CDK2 complex 1 CDK2
fibrinogen complex 1 THBS1
cyclin A1-CDK1 complex 1 CDK1
cyclin A2-CDK1 complex 1 CDK1
cyclin B1-CDK1 complex 2 CCNB1, CDK1
vacuolar membrane 2 SLC36A1, SLC3A1
clathrin-sculpted gamma-aminobutyric acid transport vesicle membrane 1 GAD1
cyclin A2-CDK2 complex 1 CDK2
cyclin A1-CDK2 complex 1 CDK2
activin receptor complex 1 TGFBR1
transforming growth factor beta ligand-receptor complex 1 TGFBR1
4-aminobutyrate transaminase complex 1 ABAT
homomeric SMAD protein complex 1 SMAD2


文献列表

  • Pangzhen Zhang, Nathaniel Quan En Chua, Simon Dang, Ashleigh Davis, Kah Wee Chong, Stephen S Prime, Nicola Cirillo. Molecular Mechanisms of Malignant Transformation of Oral Submucous Fibrosis by Different Betel Quid Constituents-Does Fibroblast Senescence Play a Role?. International journal of molecular sciences. 2022 Jan; 23(3):. doi: 10.3390/ijms23031637. [PMID: 35163557]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Jiao Wu, He Zhang, Shijie Wang, Langxing Yuan, Paul Grünhofer, Lukas Schreiber, Yinglang Wan. Tissue-specific and maturity-dependent distribution of pyridine alkaloids in Areca triandra. Journal of plant research. 2019 Jul; 132(4):531-540. doi: 10.1007/s10265-019-01115-9. [PMID: 31127431]
  • Felix Kern, Klaus T Wanner. Screening oxime libraries by means of mass spectrometry (MS) binding assays: Identification of new highly potent inhibitors to optimized inhibitors γ-aminobutyric acid transporter 1. Bioorganic & medicinal chemistry. 2019 04; 27(7):1232-1245. doi: 10.1016/j.bmc.2019.02.015. [PMID: 30777661]
  • Kinga Sałat, Adrian Podkowa, Natalia Malikowska, Felix Kern, Jörg Pabel, Ewelina Wojcieszak, Katarzyna Kulig, Klaus T Wanner, Beata Strach, Elżbieta Wyska. Novel, highly potent and in vivo active inhibitor of GABA transporter subtype 1 with anticonvulsant, anxiolytic, antidepressant and antinociceptive properties. Neuropharmacology. 2017 02; 113(Pt A):331-342. doi: 10.1016/j.neuropharm.2016.10.019. [PMID: 27771379]
  • Adrian A Franke, Xingnan Li, Jennifer F Lai. Pilot study of the pharmacokinetics of betel nut and betel quid biomarkers in saliva, urine, and hair of betel consumers. Drug testing and analysis. 2016 Oct; 8(10):1095-1099. doi: 10.1002/dta.1912. [PMID: 26619803]
  • Hongli Yu, Lijuan Tang, Hao Wu, Kuilong Wang, Baochang Cai, Xingde Zhang, Chengchao Zhang, Yunzhi Yin. Determination of contents of four alkaloids in Pericarpium arecae by quantitative analysis of multi-components by single-marker. Pakistan journal of pharmaceutical sciences. 2016 Jul; 29(4):1269-74. doi: ". [PMID: 27393441]
  • Rune Nørgaard Rasmussen, Candela Lagunas, Jakob Plum, René Holm, Carsten Uhd Nielsen. Interaction of GABA-mimetics with the taurine transporter (TauT, Slc6a6) in hyperosmotic treated Caco-2, LLC-PK1 and rat renal SKPT cells. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2016 Jan; 82(?):138-46. doi: 10.1016/j.ejps.2015.11.020. [PMID: 26631583]
  • Xiaofeng Ma, Hodney Lubin, Enikő Ioja, Orsolya Kékesi, Ágnes Simon, Ágota Apáti, Tamás I Orbán, László Héja, Julianna Kardos, István E Markó. Straightforward and effective synthesis of γ-aminobutyric acid transporter subtype 2-selective acyl-substituted azaspiro[4.5]decanes. Bioorganic & medicinal chemistry letters. 2016 Jan; 26(2):417-423. doi: 10.1016/j.bmcl.2015.11.100. [PMID: 26706177]
  • Miriam Sindelar, Toni A Lutz, Marilena Petrera, Klaus T Wanner. Focused pseudostatic hydrazone libraries screened by mass spectrometry binding assay: optimizing affinities toward γ-aminobutyric acid transporter 1. Journal of medicinal chemistry. 2013 Feb; 56(3):1323-40. doi: 10.1021/jm301800j. [PMID: 23336362]
  • Maurizio Coppola, Raffaella Mondola. Potential action of betel alkaloids on positive and negative symptoms of schizophrenia: a review. Nordic journal of psychiatry. 2012 Apr; 66(2):73-8. doi: 10.3109/08039488.2011.605172. [PMID: 21859398]
  • Jingsong Yuan, Dajian Yang, Yonghong Liang, Wenping Gao, Zhipeng Ren, Wei Zeng, Baorong Wang, Jian Han, Dean Guo. Alkaloids from areca (betel) nuts and their effects on human sperm motility in vitro. Journal of food science. 2012 Apr; 77(4):T70-8. doi: 10.1111/j.1750-3841.2012.02653.x. [PMID: 22515256]
  • C Suñol, Z Babot, R Cristòfol, U Sonnewald, H S Waagepetersen, A Schousboe. A possible role of the non-GAT1 GABA transporters in transfer of GABA from GABAergic to glutamatergic neurons in mouse cerebellar neuronal cultures. Neurochemical research. 2010 Sep; 35(9):1384-90. doi: 10.1007/s11064-010-0196-1. [PMID: 20512624]
  • Mark R Faust, Georg Höfner, Jörg Pabel, Klaus T Wanner. Azetidine derivatives as novel gamma-aminobutyric acid uptake inhibitors: synthesis, biological evaluation, and structure-activity relationship. European journal of medicinal chemistry. 2010 Jun; 45(6):2453-66. doi: 10.1016/j.ejmech.2010.02.029. [PMID: 20219271]
  • László Héja, Péter Barabás, Gabriella Nyitrai, Katalin A Kékesi, Bálint Lasztóczi, Orsolya Toke, Gábor Tárkányi, Karsten Madsen, Arne Schousboe, Arpád Dobolyi, Miklós Palkovits, Julianna Kardos. Glutamate uptake triggers transporter-mediated GABA release from astrocytes. PloS one. 2009 Sep; 4(9):e7153. doi: 10.1371/journal.pone.0007153. [PMID: 19777062]
  • Andrea Kragler, Georg Höfner, Klaus T Wanner. Synthesis and biological evaluation of aminomethylphenol derivatives as inhibitors of the murine GABA transporters mGAT1-mGAT4. European journal of medicinal chemistry. 2008 Nov; 43(11):2404-11. doi: 10.1016/j.ejmech.2008.01.005. [PMID: 18395300]
  • Anna Palló, Akos Bencsura, László Héja, Tamás Beke, András Perczel, Julianna Kardos, Agnes Simon. Major human gamma-aminobutyrate transporter: in silico prediction of substrate efficacy. Biochemical and biophysical research communications. 2007 Dec; 364(4):952-8. doi: 10.1016/j.bbrc.2007.10.108. [PMID: 17967412]
  • Sarbani Giri, Jeffrey R Idle, Chi Chen, T Mark Zabriskie, Kristopher W Krausz, Frank J Gonzalez. A metabolomic approach to the metabolism of the areca nut alkaloids arecoline and arecaidine in the mouse. Chemical research in toxicology. 2006 Jun; 19(6):818-27. doi: 10.1021/tx0600402. [PMID: 16780361]
  • Alan Sarup, Orla Miller Larsson, Tina Bolvig, Bente Frølund, Povl Krogsgaard-Larsen, Arne Schousboe. Effects of 3-hydroxy-4-amino-4,5,6,7-tetrahydro-1,2-benzisoxazol (exo-THPO) and its N-substituted analogs on GABA transport in cultured neurons and astrocytes and by the four cloned mouse GABA transporters. Neurochemistry international. 2003 Sep; 43(4-5):445-51. doi: 10.1016/s0197-0186(03)00033-0. [PMID: 12742090]
  • M-E Ruiz-Tachiquín, E Sánchez-Lemus, L-E Soria-Jasso, J-A Arias-Montaño, A Ortega. Gamma-aminobutyric acid transporter (BGT-1) expressed in human astrocytoma U373 MG cells: pharmacological and molecular characterization and phorbol ester-induced inhibition. Journal of neuroscience research. 2002 Jul; 69(1):125-32. doi: 10.1002/jnr.10258. [PMID: 12111824]
  • N S Chu. Effects of Betel chewing on the central and autonomic nervous systems. Journal of biomedical science. 2001 May; 8(3):229-36. doi: 10.1007/bf02256596. [PMID: 11385294]
  • L J Knutsen, K E Andersen, J Lau, B F Lundt, R F Henry, H E Morton, L Naerum, H Petersen, H Stephensen, P D Suzdak, M D Swedberg, C Thomsen, P O Sørensen. Synthesis of novel GABA uptake inhibitors. 3. Diaryloxime and diarylvinyl ether derivatives of nipecotic acid and guvacine as anticonvulsant agents. Journal of medicinal chemistry. 1999 Sep; 42(18):3447-62. doi: 10.1021/jm981027k. [PMID: 10479278]
  • C K Wang, C H Peng. The mutagenicities of alkaloids and N-nitrosoguvacoline from betel quid. Mutation research. 1996 Aug; 360(3):165-71. doi: 10.1016/s0165-1161(96)90013-8. [PMID: 8692215]
  • T G Dhar, L A Borden, S Tyagarajan, K E Smith, T A Branchek, R L Weinshank, C Gluchowski. Design, synthesis and evaluation of substituted triarylnipecotic acid derivatives as GABA uptake inhibitors: identification of a ligand with moderate affinity and selectivity for the cloned human GABA transporter GAT-3. Journal of medicinal chemistry. 1994 Jul; 37(15):2334-42. doi: 10.1021/jm00041a012. [PMID: 8057281]
  • E Falch, B S Meldrum, P Krogsgaard-Larsen. GABA uptake inhibitors. Synthesis and effects on audiogenic seizures of ester prodrugs of nipecotic acid, guvacine and cis-4-hydroxynipecotic acid. Drug design and delivery. 1987 Sep; 2(1):9-21. doi: . [PMID: 3509345]
  • D Lodge, G A Johnston, D R Curtis, S J Brand. Effects of the Areca nut constituents arecaidine and guvacine on the action of GABA in the cat central nervous system. Brain research. 1977 Nov; 136(3):513-22. doi: 10.1016/0006-8993(77)90075-0. [PMID: 922499]
  • R E Olver. Ion transport and water flow in the mammalian lung. Ciba Foundation symposium. 1976; ?(38):199-200. doi: 10.1002/9780470720202.ch12. [PMID: 7441]